Leather Pilot Bags

When you’re travelling, you need a copilot you can trust. Whether you’re meandering through the midwest by plane, or coasting along Highway 1 by car, our leather pilot bags are tough enough to withstand the journey with you. Take one on your next quest to indicate your character—relentless in pursuit, steadfast in search, and courageous to the core. Leather pilot bags embody all of that and more, they’re just waiting to join you.

A pilot bag, or flight bag, is a structured, top-handled bag with a flat profile, based on the bags airline crews carry. Ours are full-grain leather: the top layer of the hide, left whole, so it gets better with wear instead of peeling or cracking. The Roosevelt bags are water buffalo leather and the Walker is cow leather. We design them in Matthews, North Carolina, and have made them since 2009 with partner workshops in India and Mexico. Prices run from $339.95 to $374.95.

Which Pilot Bag Fits How You Travel

Prices, ratings and review counts as of October 2026. Each product page shows the current price, color options and stock. The Roosevelt bags also come in Amber Brown and Dark Oak, and the Walker in Rustic Tan and Vintage Oak.

How to Choose

• By laptop. The Roosevelt Flight Bag has a 13.5 x 8 inch sleeve and the Roosevelt Large Flight Bag a 15.5 x 8.5 inch sleeve. The Walker has no laptop sleeve. Measure your laptop before you pick.
• By weight. The Walker is 2 lb 15 oz, the Roosevelt Flight Bag 4 lb 14 oz and the Roosevelt Large 5 lb 14 oz.
• By material. Water buffalo leather (Roosevelt) is thick, with a pronounced grain and a deep patina. Cow leather (Walker) is a little smoother and lighter. The Roosevelt bags have a canvas lining and antique brass hardware.
• By use. A flight bag is flatter than a duffle and more casual than a briefcase. If you carry a laptop every day, also compare messenger bags and briefcases. For a few days away, see duffle bags.

Discover Our Leather Pilot Bags

Embark on a new endeavor with one of our leather pilot bags, and finally find the function and style you’ve been looking for when packing. For a rugged, hefty option that’s ready to take the ride, shop our Roosevelt Buffalo Leather Pilot Bag. Lined with a canvas interior, this secure bag is prepared to support your journey, and its antique brass hardware and exterior buckled pockets give it shape and room for small essentials, while the interior sleeve holds a laptop. For a lighter, no-frills option, browse our Walker Leather Pilot Bag, available in Rustic Tan and Vintage Oak. Easily carry it over the shoulder or store it under the seat for a durable bag that can handle the stress of today’s travel. Its antique brass button snaps keep your belongings safe and keep you moving without hassle. If you love our pilot bags, be sure to explore messenger bags for comparable comfort and packing capabilities.

How to Care for Leather Pilot Bags

If you’re getting the best use of your leather pilot bags, they’re bound to see some regular wear and tear, so caring for them is key. Check out our leather care products for excellent leather cleaner and conditioner, suited for full-grain leather pilot bags. Wondering what to do if your bag got wet? Read the next three steps you should take on our blog. Or, learn how you can remove stains from leather pilot bags with ease—these tricks will take care of anything from water to grease and oil stains. Whatever you do, just make sure your precious cargo is protected and cleaned from time to time.

The best thing about travelling is the unexpected—you don’t always know where you’ll end up or where the winding road will take you. The unplanned is often more fun than the planned anyway. Make sure you’re prepared for any excursion and shop all of our leather travel bags to find the right fit for your adventurous flair. And don’t forget to capture the moments. Bring along your photo gear in one of our leather camera bags, or jot down your field notes in a journal bound by a leather cover. Speaking of bounds—your opportunities are boundless, so grab your leather pilot bags and start looking for the next place to land.

Before You Buy

• What is a flight bag?
• Types of travel bags
• Full-grain vs. top-grain leather
• 3 steps to care for your leather bag

Shop More

Leather travel bags · Messenger bags · Briefcases · Duffle bags · All leather bags for men

Frequently Asked Questions

1. What makes leather pilot bags the ideal travel companion?
   Our leather pilot bags are crafted with the traveler in mind. Durable, stylish, and functional, we’ve designed these bags to be your co-pilot on any journey. With features like antique brass hardware, exterior buckled pockets, a canvas-lined interior and, on the Roosevelt models, a laptop sleeve, leather pilot bags are the embodiment of quality and craftsmanship.
2. How do I choose the right leather pilot bag for my needs?
   Start with what you carry. For a laptop, choose the Roosevelt Large Flight Bag or the Roosevelt Flight Bag. For a lighter bag without a laptop sleeve, choose the Walker Leather Pilot Bag. Consider your travel needs, storage preferences, and personal style.
3. What is a leather pilot bag?
   A pilot bag, or flight bag, is a structured, top-handled bag with a flat profile, based on the bags airline crews carry. See what is a flight bag.
4. Will a leather pilot bag fit my laptop?
   The Roosevelt Flight Bag has a 13.5 x 8 inch laptop sleeve and the Roosevelt Large Flight Bag has a 15.5 x 8.5 inch sleeve. The Walker Vintage Pilot Bag has no laptop sleeve. Measure your laptop and compare it to the sleeve on the product page.
5. What is the difference between the Roosevelt and Walker pilot bags?
   The Roosevelt is full-grain water buffalo leather with a canvas lining, a laptop sleeve and antique brass hardware, and weighs 4 lb 14 oz. The Walker is full-grain cow leather, has no laptop sleeve, and weighs 2 lb 15 oz.
6. How do leather pilot bags differ from other travel bags?
   Leather pilot bags offer a specialized blend of rugged durability and elegant aesthetics that make them unique in the world of travel accessories. With features like exterior buckled pockets and a canvas-lined interior, these bags are tailored for the traveler who values both form and function. Unlike standard travel bags, our leather pilot bags tell a story of adventure, resilience, and character.
7. Where can I use my leather pilot bag?
   Whether you're flying the friendly skies or hitting the highway, our leather pilot bags are ready to accompany you. Designed to withstand the rigors of travel, they're equally suited for business trips and wild explorations. Your leather pilot bag isn't just luggage; it's a symbol of your adventurous spirit.
8. What kind of care do leather pilot bags require?
   Proper care ensures that your leather pilot bag remains a reliable travel companion, ready to journey with you for years to come. Regular cleaning and conditioning with our specialized leather care products will keep them looking their best. From stain removal to drying procedures, you can find comprehensive care instructions on our blog.
9. Where are Buffalo Jackson pilot bags made?
   We design them in Matthews, North Carolina. The Roosevelt pilot bags are made in India and the Walker in Mexico.
10. Why invest in Buffalo Jackson's leather pilot bags?
    When you choose one of our leather pilot bags, you're investing in more than just a travel accessory. You're embracing an ethos of relentless pursuit, steadfast exploration, and boundless opportunity. Each leather pilot bag is a testament to your character and a reflection of your passion for life and adventure. Explore our collection and find the leather pilot bag that calls to you.

Updated October 2026. Product details, prices, and links on this page are reviewed by the Buffalo Jackson team.